There's nothing inherently difficult with a 1031 other than some compressed time lines that force you to shop hard early and decisively. 

What obstacles or barriers have you encountered.

Priyanka,There is some good advice in here.

I have a single woman in her 60’s who has rented it for some time.

@Edmund Fontana I assume so professionals will chime in here too, but this is my understanding.I just got done with my taxes so I will use the percents that I am familiar with in my market.Say you invest 100K into 500K of rentals.

Hey all,I have an accountant but I like to throw my general questions in here.

I don't see anything in here for sales costs like 6% agent commissions, closing costs, etc. 

Finally, with the use of Trusts while establishing these structures you can add a level of anonymity by removing your name from public record.You face several different types of liability inherent with house hacking.

Since then I’ve bought 3 more SFH’s with my biggest obstacle being my full time job in the military.

Her long-term renters were moving out and in her words, "It's time to let this one go".